“What does it mean?????????????” John Ashbery wrote more than fifty years ago in The Tennis Court Oath, his second book of poems. The very exuberance of the punctuation may have sounded a note of caution for any readers who were looking for quick answers. (Perhaps thirteen question marks were an unlucky omen.) Since then, though, his work has been translated into twenty-five languages, and many would claim that a typical Ashbery poem speaks twenty-five languages. Even the poet has cast quizzical side-glances at his perplexing career. “I tell myself it all seems like fun and will work out in the end,” he noted in 1987. “I expect I will be asked a question I can answer and then handed a big prize. They’re working on it.” Several big prizes later, as he approaches his ninetieth birthday, Ashbery is still working on “it,” still wondering what “it” is. In 2006, when New York’s city council declared April 7 John Ashbery Day, the poet couldn’t resist asking: “But what does a John Ashbery Day mean? Are people going to stop and pause and think for a minute?”

Maybe we could use that sixty-second silence to cast our minds back to the time before he made a name for himself. Ashbery was nearly fifty when Self-Portrait in a Convex Mirror, his seventh collection, finally brought him widespread acclaim in 1975, and although he already had the makings of an audience, he didn’t quite have a public. Some aspects of his youth, particularly the early 1950s in New York, have received attention — David Lehman’s sprightly study The Last Avant-Garde comes to mind — but Karin Roffman’s new book is the first comprehensive biography of his childhood. The Songs We Know Best draws on a great deal of unpublished material: a thousand-page diary Ashbery kept between the ages of thirteen and sixteen; drafts of almost all his adolescent writing; interviews with several close friends; and more than a hundred hours of conversation with the poet himself. “I’m sometimes kind of jealous of my work,” Ashbery once observed. “It keeps getting all the attention and I’m not. After all, I wrote it.” Roffman redresses the balance while also keeping a close eye on the work; her aim, in fact, is to reveal “an intertwining of life and art in extraordinarily intimate ways.”

The biography is certainly revealing, but it’s noteworthy that the poem from which Roffman takes her title raises some doubts about intimacy: “Or do ya still think that I’m somebody else?” Ashbery has said that “artists are no fun once they have been discovered.” Roffman’s portrait of the artist as a young man made me think of what the young man said to his friend and fellow poet Kenneth Koch when they were undergraduates at Harvard in the 1940s: “I try to erect a smokescreen near the end of my poems so I can withdraw unperceived — I never like to be around for the last line.”

The songs, poems, and lives we know best frequently tell us how little we know. Although Ashbery is fascinated by biography — Roffman says that his enthusiasm for the mode is “at the service of his desire to become a better reader of the writers he liked” — many of his favorite writers drew attention to the limited ability of life writing to explain either the self or the work. As Gertrude Stein, one of Ashbery’s first literary loves, wrote in Everybody’s Autobiography: “Identity is funny being yourself is funny as you are never yourself to yourself except as you remember yourself and then of course you do not believe yourself.” Ashbery’s work — often funny-amusing as well as funny-peculiar — has flourished in such knots of conviction and incredulity. In the early poem “The Picture of Little J. A. in a Prospect of Flowers,” he is inclined to call the “comic version of myself” — that is, the childhood self he’s recalling — the “true one,” and part of the truth of this springs from the comedy of imagining that you have a self to call your own. (“My life story,” he writes elsewhere: “I am toying with the idea.”)

The question so often asked of Ashbery’s poetry — “What does it mean?????????????” — is one that the poetry asks of his life, although neither the question nor any possible answer to it is ever allowed to steal the show. He is not so much concerned with what one’s life story adds up to as with what it may subtract from.